JP2010535177A - ゾピクロンの分割方法および中間化合物 - Google Patents
ゾピクロンの分割方法および中間化合物 Download PDFInfo
- Publication number
- JP2010535177A JP2010535177A JP2010518689A JP2010518689A JP2010535177A JP 2010535177 A JP2010535177 A JP 2010535177A JP 2010518689 A JP2010518689 A JP 2010518689A JP 2010518689 A JP2010518689 A JP 2010518689A JP 2010535177 A JP2010535177 A JP 2010535177A
- Authority
- JP
- Japan
- Prior art keywords
- acetyl
- zopiclone
- formula
- salt
- aspartate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 49
- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 title claims description 49
- 229960000820 zopiclone Drugs 0.000 title description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 150000001413 amino acids Chemical class 0.000 claims abstract description 23
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 13
- GBBSUAFBMRNDJC-INIZCTEOSA-N eszopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-INIZCTEOSA-N 0.000 claims description 67
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
- OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 claims description 26
- 229940024606 amino acid Drugs 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- RFMMMVDNIPUKGG-YFKPBYRVSA-N N-acetyl-L-glutamic acid Chemical compound CC(=O)N[C@H](C(O)=O)CCC(O)=O RFMMMVDNIPUKGG-YFKPBYRVSA-N 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- OTCCIMWXFLJLIA-SCSAIBSYSA-N (2r)-2-acetamidobutanedioic acid Chemical compound CC(=O)N[C@@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-SCSAIBSYSA-N 0.000 claims description 15
- RFMMMVDNIPUKGG-RXMQYKEDSA-N (2r)-2-acetamidopentanedioic acid Chemical compound CC(=O)N[C@@H](C(O)=O)CCC(O)=O RFMMMVDNIPUKGG-RXMQYKEDSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 6
- WHZRCUIISKRTJL-UHFFFAOYSA-N [2-(6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl)-2-oxoethyl] hexanoate Chemical compound C1C(F)C2=CC(=O)C=CC2(C)C2C1C1CC(C)C(C(=O)COC(=O)CCCCC)C1(C)CC2O WHZRCUIISKRTJL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- XUYPXLNMDZIRQH-ZCFIWIBFSA-N N-acetyl-D-methionine Chemical compound CSCC[C@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-ZCFIWIBFSA-N 0.000 claims description 4
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 150000001298 alcohols Chemical group 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 230000006340 racemization Effects 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- 229940049906 glutamate Drugs 0.000 claims 2
- 229930195712 glutamate Natural products 0.000 claims 2
- CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical compound OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims 1
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 claims 1
- 229930182818 D-methionine Natural products 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 15
- 238000004296 chiral HPLC Methods 0.000 description 14
- 229960001578 eszopiclone Drugs 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 238000000634 powder X-ray diffraction Methods 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- -1 5-chloro-2-pyridyl Chemical group 0.000 description 9
- 239000002253 acid Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 5
- 239000012265 solid product Substances 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GBBSUAFBMRNDJC-UHFFFAOYSA-N zopiclone Chemical compound C1CN(C)CCN1C(=O)OC1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- ZMJIPNACONXBCG-UHFFFAOYSA-N 7h-pyrrolo[3,4-b]pyrazine Chemical group C1=CN=C2CN=CC2=N1 ZMJIPNACONXBCG-UHFFFAOYSA-N 0.000 description 1
- LKBBROWNGCRSBP-UHFFFAOYSA-N CC(NC(C(O)=O)N)=O Chemical compound CC(NC(C(O)=O)N)=O LKBBROWNGCRSBP-UHFFFAOYSA-N 0.000 description 1
- 229930195713 D-glutamate Natural products 0.000 description 1
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HFDGGXUVSFYTLN-UHFFFAOYSA-N c1ncc2[nH]ccnc12 Chemical compound c1ncc2[nH]ccnc12 HFDGGXUVSFYTLN-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07380226A EP2020403A1 (de) | 2007-08-02 | 2007-08-02 | Verfahren zur Auflösung von Zopiclon und Zwischenprodukten |
| PCT/EP2008/060115 WO2009016251A1 (en) | 2007-08-02 | 2008-08-01 | Process for the resolution of zopiclone and intermediate compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2010535177A true JP2010535177A (ja) | 2010-11-18 |
Family
ID=38871700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010518689A Withdrawn JP2010535177A (ja) | 2007-08-02 | 2008-08-01 | ゾピクロンの分割方法および中間化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7772396B2 (de) |
| EP (2) | EP2020403A1 (de) |
| JP (1) | JP2010535177A (de) |
| KR (1) | KR20100044241A (de) |
| CN (1) | CN101772475B (de) |
| AT (1) | ATE551312T1 (de) |
| AU (1) | AU2008281717A1 (de) |
| CA (1) | CA2695254A1 (de) |
| ES (1) | ES2385120T3 (de) |
| HR (1) | HRP20120306T1 (de) |
| IL (1) | IL203557A (de) |
| MX (1) | MX2010001229A (de) |
| NZ (1) | NZ583097A (de) |
| PL (1) | PL2183201T3 (de) |
| RU (1) | RU2010107453A (de) |
| SI (1) | SI2183201T1 (de) |
| WO (1) | WO2009016251A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015119057A1 (ja) * | 2014-02-06 | 2015-08-13 | 宇部興産株式会社 | インドリン化合物の製造方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7476737B2 (en) * | 2005-09-05 | 2009-01-13 | Dr. Reddy's Laboratories Limited | Eszopiclone process |
| US8163913B2 (en) * | 2005-12-19 | 2012-04-24 | Sicor Inc. | Forms of tiotropium bromide and processes for preparation thereof |
| CN101607961B (zh) * | 2008-06-18 | 2011-08-10 | 天津天士力集团有限公司 | 一种右佐匹克隆结晶及其组合物 |
| EP2345654A1 (de) * | 2010-01-05 | 2011-07-20 | LEK Pharmaceuticals d.d. | Eszopiclon-Teilchen und Verfahren zu deren Herstellung |
| CN103193779B (zh) * | 2012-01-05 | 2016-04-20 | 成都弘达药业有限公司 | 一种右佐匹克隆的制备方法 |
| DE102020205560B4 (de) | 2020-04-30 | 2022-05-25 | Zettl Interieur Gmbh | Flexible atemschutzmaske und deren verwendung |
| CN113214267B (zh) * | 2021-05-08 | 2022-06-28 | 上海中西三维药业有限公司 | 一种制备纯净且光学富集的右佐匹克隆精制方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA04285A (fr) | 1972-01-07 | 1979-12-31 | Rhone Poulenc Sa | Nouveaux dérivés de la pyrrolo (3,4-b) pyrazine et leur préparation. |
| FR2671800B1 (fr) | 1991-01-17 | 1993-03-12 | Rhone Poulenc Rorer Sa | Derive de la 5h-pyrrolo[3,4-b]pyrazine optiquement actif, sa preparation et les compositions pharmaceutiques qui le contiennent. |
| ES2203319B1 (es) | 2002-04-03 | 2005-03-01 | Universidad De Oviedo | Nuevos carbonatos opticamente activos como intermedios en la sintesis de (+)-zopiclona. |
| CA2548917C (en) | 2003-12-11 | 2014-09-23 | Sepracor Inc. | Combination of a sedative and a neurotransmitter modulator, and methods for improving sleep quality and treating depression |
| US20050267176A1 (en) | 2004-02-18 | 2005-12-01 | Sepracor Inc. | Dopamine-agonist combination therapy for improving sleep quality |
| AU2005231490B2 (en) | 2004-04-05 | 2011-05-19 | Sunovion Pharmaceuticals Inc. | Methods of treatment using eszopiclone |
| WO2006136866A1 (en) | 2005-06-21 | 2006-12-28 | Generics [Uk] Limited | Process for enantiomeric separation of zopiclone |
| US7476737B2 (en) | 2005-09-05 | 2009-01-13 | Dr. Reddy's Laboratories Limited | Eszopiclone process |
| EP1984368A2 (de) | 2006-01-17 | 2008-10-29 | Glenmark Pharmaceuticals Limited | Verbessertes verfahren zur herstellung eines optisch aktiven 5h-pyrrolo[3,4-b)pyrazinderivats |
| WO2007088073A1 (en) | 2006-02-03 | 2007-08-09 | Synthon B.V. | Zopiclone resolution using l-tartaric acid |
| US20080027223A1 (en) | 2006-03-23 | 2008-01-31 | Teva Pharmaceutical Industries Ltd. | Polymorphs of eszopiclone malate |
| EP2007768A2 (de) | 2006-04-20 | 2008-12-31 | Teva Pharmaceutical Industries Ltd | Verfahren zur zubereitung von eszopiclon-kristallinform a, im wesentlichen reines eszopiclon und optisch angereichertes eszopiclon |
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2007
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- 2007-10-03 US US11/866,584 patent/US7772396B2/en not_active Expired - Fee Related
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2008
- 2008-08-01 SI SI200830601T patent/SI2183201T1/sl unknown
- 2008-08-01 WO PCT/EP2008/060115 patent/WO2009016251A1/en active Application Filing
- 2008-08-01 ES ES08786735T patent/ES2385120T3/es active Active
- 2008-08-01 CN CN200880101463XA patent/CN101772475B/zh not_active Expired - Fee Related
- 2008-08-01 PL PL08786735T patent/PL2183201T3/pl unknown
- 2008-08-01 AT AT08786735T patent/ATE551312T1/de active
- 2008-08-01 EP EP08786735A patent/EP2183201B1/de active Active
- 2008-08-01 AU AU2008281717A patent/AU2008281717A1/en not_active Abandoned
- 2008-08-01 KR KR1020107004730A patent/KR20100044241A/ko not_active Application Discontinuation
- 2008-08-01 NZ NZ583097A patent/NZ583097A/en not_active IP Right Cessation
- 2008-08-01 JP JP2010518689A patent/JP2010535177A/ja not_active Withdrawn
- 2008-08-01 CA CA2695254A patent/CA2695254A1/en not_active Abandoned
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- 2008-08-01 RU RU2010107453/04A patent/RU2010107453A/ru not_active Application Discontinuation
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2010
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- 2010-07-02 US US12/830,147 patent/US7968712B2/en not_active Expired - Fee Related
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015119057A1 (ja) * | 2014-02-06 | 2015-08-13 | 宇部興産株式会社 | インドリン化合物の製造方法 |
| JPWO2015119057A1 (ja) * | 2014-02-06 | 2017-03-23 | 宇部興産株式会社 | インドリン化合物の製造方法 |
| US9643921B2 (en) | 2014-02-06 | 2017-05-09 | Ube Industries, Ltd. | Method for producing indoline compound |
| US9932308B2 (en) | 2014-02-06 | 2018-04-03 | Ube Industries, Ltd. | Method for producing indoline compound |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2010107453A (ru) | 2011-09-10 |
| CA2695254A1 (en) | 2009-02-05 |
| MX2010001229A (es) | 2010-03-04 |
| US7772396B2 (en) | 2010-08-10 |
| AU2008281717A1 (en) | 2009-02-05 |
| US20090036681A1 (en) | 2009-02-05 |
| HRP20120306T1 (hr) | 2012-04-30 |
| PL2183201T3 (pl) | 2012-09-28 |
| CN101772475A (zh) | 2010-07-07 |
| KR20100044241A (ko) | 2010-04-29 |
| EP2020403A1 (de) | 2009-02-04 |
| NZ583097A (en) | 2011-03-31 |
| ATE551312T1 (de) | 2012-04-15 |
| US20100274018A1 (en) | 2010-10-28 |
| WO2009016251A1 (en) | 2009-02-05 |
| IL203557A (en) | 2014-11-30 |
| EP2183201B1 (de) | 2012-03-28 |
| CN101772475B (zh) | 2013-11-06 |
| ES2385120T3 (es) | 2012-07-18 |
| EP2183201A1 (de) | 2010-05-12 |
| SI2183201T1 (sl) | 2012-05-31 |
| US7968712B2 (en) | 2011-06-28 |
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